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Cheap flights from Orlando to Chicago from $34

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Orlando to Chicago departing on 12/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Orlando to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Orlando to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Orlando to Chicago.

Cheap last minute flights

Planning a quick getaway from Orlando to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Orlando to Chicago

Find recent round-trip train or bus tickets from Orlando to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$65Frontier
Find Deal
Fri, Jan 31 - Sun, Feb 2
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
$68Frontier
Find Deal
Fri, Jan 24 - Mon, Jan 27
11:45 am - 11:35 pmMCO-ORD
12h 50m1 stop
5:28 pm - 9:37 pmORD-MCO
3h 09mnonstop
Wed, Jan 15 - Mon, Jan 20
11:45 am - 11:34 pmMCO-ORD
12h 49m1 stop
4:18 pm - 8:15 pmORD-MCO
2h 57mnonstop
Wed, Jan 15 - Sun, Jan 19
8:00 am - 9:52 amSFB-RFD
2h 52mnonstop
10:42 am - 2:25 pmRFD-SFB
2h 43mnonstop
$101Allegiant Air
Find Deal
Fri, Jan 24 - Mon, Jan 27
9:24 am - 11:32 amMCO-ORD
3h 08mnonstop
12:37 pm - 4:24 pmORD-MCO
2h 47mnonstop
$104Spirit Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
9:24 am - 11:32 amMCO-ORD
3h 08mnonstop
6:06 pm - 9:58 pmORD-MCO
2h 52mnonstop
$114Spirit Airlines
Find Deal
Thu, Jan 30 - Mon, Feb 3
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
$153Southwest
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Tue, Jan 28 - Tue, Jan 28
8:00 am - 9:54 amSFB-RFD
2h 54mnonstop
10:44 am - 2:25 pmRFD-SFB
2h 41mnonstop
$157Allegiant Air
Find Deal
Tue, Dec 24 - Tue, Dec 31
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
2:35 pm - 6:10 pmMDW-MCO
2h 35mnonstop
$164Southwest
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Fri, Jan 10 - Sat, Jan 11
4:00 pm - 5:54 pmMCO-MDW
2h 54mnonstop
$34Frontier
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Tue, Dec 17
7:50 pm - 9:53 pmMCO-ORD
3h 03mnonstop
$37Spirit Airlines
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Thu, Dec 19
7:50 pm - 9:53 pmMCO-ORD
3h 03mnonstop
$38Spirit Airlines
Find Deal
Thu, Dec 19
4:00 pm - 5:54 pmMCO-MDW
2h 54mnonstop
$39Frontier
Find Deal
Tue, Dec 17
2:35 pm - 4:38 pmMCO-ORD
3h 03mnonstop
$79United Airlines
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Wed, Jan 22
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
$79Southwest
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Tue, Jan 14
4:10 pm - 6:16 pmMCO-ORD
3h 06mnonstop
$85United Airlines
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Fri, Feb 28
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$85Southwest
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Thu, Jan 9
7:50 am - 10:02 amMCO-ORD
3h 12mnonstop
$105American Airlines
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Tue, Dec 24
7:00 am - 9:16 amMCO-ORD
3h 16mnonstop
$167American Airlines
Find Deal
Thu, Dec 12
5:02 am - 4:06 pmMCO-ORD
12h 04m1 stop
9:35 am - 1:30 pmORD-MCO
2h 55mnonstop
Tue, Dec 10 - Sun, Dec 15
12:31 pm - 5:40 pmMCO-ORD
6h 09m1 stop
1:13 pm - 5:16 pmORD-MCO
3h 03mnonstop
$150Spirit Airlines
Find Deal
Tue, Dec 10 - Tue, Dec 17
7:30 am - 9:54 amMCO-ORD
3h 24mnonstop
9:35 am - 1:30 pmORD-MCO
2h 55mnonstop
$204Frontier
Find Deal
Mon, Dec 9 - Thu, Dec 12
11:30 am - 10:38 pmMCO-ORD
12h 08m1 stop
10:29 am - 2:24 pmORD-MCO
2h 55mnonstop
$213Frontier
Find Deal
Mon, Dec 9 - Wed, Dec 18
7:12 am - 9:30 amMCO-ORD
3h 18mnonstop
7:13 pm - 11:01 pmORD-MCO
2h 48mnonstop
$289American Airlines
Find Deal
Tue, Dec 10 - Sat, Dec 14
7:12 am - 9:30 amMCO-ORD
3h 18mnonstop
5:50 pm - 9:33 pmORD-MCO
2h 43mnonstop
$309American Airlines
Find Deal
Tue, Dec 10 - Thu, Dec 12
3:35 pm - 5:25 pmMCO-MDW
2h 50mnonstop
10:05 am - 1:45 pmMDW-MCO
2h 40mnonstop
$559Southwest
Find Deal
Sun, Dec 8 - Sat, Dec 14
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
$579Southwest
Find Deal
Tue, Dec 10 - Wed, Dec 11
5:00 pm - 10:06 pmMCO-MDW
6h 06m1 stop
5:50 pm - 12:05 amMDW-MCO
5h 15m1 stop
$946Delta
Find Deal
Sat, Dec 7 - Mon, Dec 9
11:00 am - 5:01 pmMCO-MDW
7h 01m2 stops
5:50 pm - 12:05 amMDW-MCO
5h 15m1 stop
$2,271Delta
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Sat, Dec 7 - Sun, Dec 8
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
$68Frontier
Find Deal
Fri, Jan 24 - Mon, Jan 27
7:30 am - 9:54 amMCO-ORD
3h 24mnonstop
8:00 am - 11:50 amORD-MCO
2h 50mnonstop
Fri, Jan 10 - Tue, Jan 14
7:30 am - 9:52 amMCO-ORD
3h 22mnonstop
5:28 pm - 9:37 pmORD-MCO
3h 09mnonstop
$94Frontier
Find Deal
Fri, Jan 17 - Mon, Jan 20
9:24 am - 11:32 amMCO-ORD
3h 08mnonstop
12:37 pm - 4:24 pmORD-MCO
2h 47mnonstop
$104Spirit Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
12:37 pm - 4:24 pmORD-MCO
2h 47mnonstop
$115Spirit Airlines
Find Deal
Wed, Jan 15 - Mon, Jan 20
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
5:00 pm - 8:35 pmMDW-MCO
2h 35mnonstop
$158Southwest
Find Deal
Tue, Feb 4 - Sat, Feb 8
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
2:35 pm - 6:10 pmMDW-MCO
2h 35mnonstop
$164Southwest
Find Deal
Fri, Jan 10 - Sat, Jan 11
7:00 am - 9:05 amMCO-ORD
3h 05mnonstop
1:06 pm - 4:51 pmORD-MCO
2h 45mnonstop
$169American Airlines
Find Deal
Fri, Jan 17 - Mon, Jan 20
4:33 pm - 6:35 pmMCO-ORD
3h 02mnonstop
6:08 pm - 10:00 pmORD-MCO
2h 52mnonstop
$239United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
5:42 pm - 7:45 pmMCO-ORD
3h 03mnonstop
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
$277American Airlines
Find Deal
Tue, Jan 7 - Sat, Jan 11

Delta flights from Orlando to Chicago

Our best Delta deals on Orlando to Chicago flight tickets
Delta
Feb 15
MCO7:00 amOrlando
7h 42m
1 stop
ORD1:42 pmChicago O'Hare Intl
Feb 19
ORD5:15 pmChicago O'Hare Intl
6h 20m
1 stop
MCO12:35 amOrlando
Delta
Dec 14
MCO6:15 amOrlando
4h 35m
1 stop
MDW9:50 amChicago Midway
Jan 15
MDW2:08 pmChicago Midway
6h 05m
1 stop
MCO9:13 pmOrlando
Delta
Dec 14
MCO5:30 amOrlando
5h 20m
1 stop
MDW9:50 amChicago Midway
Dec 15
MDW1:30 pmChicago Midway
7h 22m
1 stop
MCO9:52 pmOrlando

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets
Frontier
Jan 31
MCO12:38 pmOrlando
3h 04m
MDW2:42 pmChicago Midway
Feb 2
MDW10:58 amChicago Midway
2h 47m
MCO2:45 pmOrlando
Frontier
Jan 24
MCO12:38 pmOrlando
3h 04m
MDW2:42 pmChicago Midway
Jan 27
MDW11:33 amChicago Midway
2h 46m
MCO3:19 pmOrlando
Frontier
Dec 12
MCO6:05 amOrlando
3h 19m
ORD8:24 amChicago O'Hare Intl
Dec 17
ORD11:24 amChicago O'Hare Intl
2h 54m
MCO3:18 pmOrlando

See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Orlando and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $118. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Orlando to Chicago during April average around $123.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $183. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Orlando to Chicago for around $257.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando to Chicago during this time can be as low as $125. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $223.

What is the cheapest Orlando to Chicago flight route?

Fly from Orlando to Chicago O'Hare Intl for the best Orlando - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Orlando is 29 days out, which is when prices tend to be around $169. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $94.

What cabin class options are available on Orlando to Chicago flights?

There are 4 cabin classes available to choose from on Orlando to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Orlando to Chicago flights?

You could potentially save up to 55% on your flight if you consider stops on a Orlando to Chicago flight.

How have Orlando to Chicago flight prices changed over time?

As of December 2024, prices for Orlando to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

Cheap Orlando to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago

Best Price Found

$34

Fastest flight time

2h 48m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Orlando in the past 72 hours is $34. The best round-trip flight deal from Orlando to Chicago found on momondo in the last 72 hours is $65.
The fastest flight from Orlando to Chicago takes 2h 48m
Direct flights go from Orlando to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

  • How far is Orlando to Chicago by plane?

    Chicago is 985.3 mi away from Orlando. 2h 52m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Orlando to Chicago?

    Prices for flights from Orlando to Chicago refresh daily.

  • How many operators does momondo search for flights from Orlando to Chicago?

  • How old do you have to be to fly from Orlando to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Orlando to Chicago?

  • What is the most popular airline from Orlando to Chicago?


Best airlines flying from Orlando to Chicago

Compare and see reviews for airlines that fly from Orlando to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $56Free CancellationRating
6.1
3,506 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $59Free CancellationRating
6.3
8,143 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $109Free CancellationRating
7.3
839 reviews
Search Allegiant Air flights
United AirlinesPriceFrom $152Free CancellationRating
7.4
9,134 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $179Free CancellationRating
8.1
4,934 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
8,682 reviews
Search Delta flights
  • Southwest Flights From Orlando to Chicago

    Southwest is one of the most popular airlines flying from Orlando to Chicago, operating 45 flights/week on average for this route. A good Southwest flight deal for Orlando to Chicago starts from $179 round-trip, up to an average price of $371. Our users have rated Southwest at 8.1/10.

  • United Airlines Flights From Orlando to Chicago

    $152 is the best United Airlines flight deal from Orlando to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $321, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,134 user reviews) flies into Chicago from Orlando 30 times in an average week so prices can vary.


Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Orlando to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Orlando to Chicago with flexible booking policies on momondo?

Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Orlando to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Orlando.

I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago